R. D. Padmaja, K. Chanda
1‑(1‑carboxymethyl)‑3‑methylimidazolium tetrafuoroborate ([Carbmmim][BF4])
(4) Pale yellow liquid. 1H NMR (400 MHz, D2O) δ 8.67 (s, 1H), 7.41(s, 1H), 7.41
(s, 1H), 5.03 (s, 2H), and 3.68 (s, 3H); 13C NMR (100 MHz, D2O) δ 172.4, 139.8,
125.6, 124.0, 52.2, 38.4; IR (KBr, cm−1): 3574, 3166, 1739, 1579, 1409, 1176 cm−1,
−
MS (FAB) m/z: 141 (M-BF4 ).
Ionic liquid‑supported Cu(II) catalyst (5) Light blue solid. 1H NMR (400 MHz, D2O)
δ 8.44 (s, 1H), 7.40 (s, 1H), 7.23 (s, 1H), and 3.89 (s, 3H); 13C NMR (100 MHz,
D2O) δ 140.4, 126.4, 126.1, 38.4, 32.1; IR (KBr, cm−1): 3519, 3169, 1654,
−
1570 cm-1, MS (FAB) m/z: 343 (M-BF4 ).
Acknowledgements The authors thank the chancellor and vice chancellor of VIT University for provid-
ing opportunity to carry out this study. Further the authors wish to thank the management of this univer-
sity for providing seed money as research grant. Kaushik Chanda thanks CSIR-Govt of India for funding
through Grant no 01(2913)/17/EMR-II.
References
1. A.R. Katritzky, C.A. Ramsden, E.F.V. Scriven, in Comprehensive Heterocyclic Chemistry III, ed. by
R.J.K. Taylor (Elsevier, Oxford, 2008)
2. J.A. Joule, K. Mills, Heterocyclic Chemistry, 5th edn. (Wiley-Blackwell, Oxford, 2010)
3. R.V.A. Orru, in Synthesis of Heterocycles via Multicomponent Reactions, ed. by E. Ruijter
(Springer, Berlin, 2010)
4. J.H. Toney, P.M. Fitzgerald, N. Grover-Sharma, S.H. Olson, W.J. May, J.G. Sundelof, D.E. Vander-
wall, K.A. Cleary, S.K. Grant, J.K. Wu, J.W. Kozarich, D.L. Pompliano, G.G. Hammond, Chem.
Biol. 5, 185 (1998)
5. S. Berghmans, J. Hunt, A. Roach, P. Goldsmith, Epilepsy Res. 75, 18 (2007)
6. R.J. Herr, Bioorg. Med. Chem. 10, 3379 (2002)
7. M.B. Hossain, D. van der Helm, R. Sanduja, M. Alam, Acta Crystallogr. C 41, 1199 (1985)
8. D.J. Carini, J.V. Duncia, P.E. Aldrich, A.T. Chiu, A.L. Johnson, M.E. Pierce, W.A. Price, J.B. San-
tella, G.J. Wells, J. Med. Chem. 34, 2525 (1991)
9. W.S. Marshall, T. Goodson, G.J. Cullinan, D. Swansonbean, K.D. Haisch, L.E. Rinkema, J.H.
Fleisch, J. Med. Chem. 30, 682 (1987)
10. Z.P. Demko, K.B. Sharpless, Org. Lett. 4, 2525 (2002)
11. D.P. Matthews, J.E. Green, A.J. Shuker, J. Comb Chem 2, 19 (2000)
12. Y.S. Gyoung, J. Shim, Y. Yamamoto, Tetrahedron Lett. 41, 4193 (2000)
13. M. Lakshmi Kantam, K. Kumar, C. Sridhar, Adv. Syn. Catal. 347, 1212 (2005)
14. W.K. Su, Z. Hong, W.G. Shan, X.X. Zhang, Eur. J. Org. Chem. 2006, 2723 (2006)
15. M. Nasrollahzadeh, Y. Bayat, D. Habibi, S. Moshaee, Tetrahedron Lett. 50, 4435 (2009)
16. P. Mani, A.K. Singh, S.K. Awasthi, Tetrahedron Lett. 55, 1879 (2014)
17. P. Mani, C. Sharma, S. Kumar, S.K. Awasthi, J. Mol. Catal. A: Chem. 392, 150 (2014)
18. V. Rama, K. Kanagaraj, K. Pitchumani, J. Org Chem. 76, 9090 (2011)
19. M.M. Heravi, A. Fazeli, H.A. Oskooie, Y.S. Beheshtiha, H. Valizadeh, Synlett 23, 2927 (2012)
20. H. Yoneyama, Y. Usami, S. Komeda, S. Harusawa, Synthesis 45, 1051 (2013)
21. B. Das, C.R. Reddy, D.N. Kumar, M. Krishnaiah, R. Narender, Synlett 2010, 391 (2010)
22. D. Amantini, R. Beleggia, F. Fringuelli, F. Pizzo, L. Vaccaro, J. Org. Chem. 69, 2896 (2004)
23. A. Khalaf-Nezhad, S. Mohammadi, RSC Adv. 3, 4362 (2013)
24. P. Sivaguru, K. Bhuvaneswari, R. Ramkumar, A. Lalitha, Tetrahedron Lett. 55, 5683 (2014)
25. D.R. Rekunge, K.S. Indalkar, G.U. Chaturbhuj, Tetrahedron Lett. 57, 5815 (2016)
26. S.K. Prajapti, A. Nagarsenkar, B.N. Babu, Tetrahedron Lett. 55, 3507 (2014)
27. N. Nowrouzi, S. Farahi, M. Irajzadeh, Tetrahedron Lett. 56, 739 (2015)
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